Advice to meet people?

Basically, I'm 27 and I haven't had a relationship serious or casual since I was a teenager. I have difficulty with self-esteem, particularly around partners, and I know that I have a lot of baggage as a person and I think that my awareness of that baggage makes me not want to intrude on other people's lives with my bullshit so that prevents me from making moves.

So, outside of dating apps do you have any advice on how to find people who can be prospective partners, or how to breach the topic with people you don't know very well. Like how the fuck do I ask the cute cashier at the store I go to every week if she's single and if I can take her on a date?
Advice to meet people?
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